Unexpected formation of 2'-deoxy-N3-(3,3,3-trifluoro-1-propenyl)uridine via a Michael-type addition to 3,3,3-trifluoropropyne

摘要

Reaction of 3,3,3-trifluoropropyne with 2'-deoxy-5-iodouridine under conditions that have previously been used to prepare 5-alkynyl-2'-deoxyuridine derivatives gave 2'-deoxy-N3-(3,3,3-trifluoro-1-propenyl)uridine. This unexpected alkylation is a result of a Michael-type addition of N3 on the pyrimidine base to the electron deficient trifluoropropyne.